HALOPEMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22ClFN4O2
Molecular Weight	416.876
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC=C(C=C1)C(=O)NCCN2CCC(CC2)N3C(=O)NC4=C3C=CC(Cl)=C4

InChI

InChIKey=NBHPRWLFLUBAIE-UHFFFAOYSA-N

InChI=1S/C21H22ClFN4O2/c22-15-3-6-19-18(13-15)25-21(29)27(19)17-7-10-26(11-8-17)12-9-24-20(28)14-1-4-16(23)5-2-14/h1-6,13,17H,7-12H2,(H,24,28)(H,25,29)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19136975 | https://www.ncbi.nlm.nih.gov/pubmed/6398861

Halopemide is a new psychotropic agent, a structural analog of the neuroleptics of the butyrophenone type but with different pharmacological and clinical properties. Preliminary clinical findings indicate that halopemide lacks the ability to induce parkinsonism and may be an effective drug in the treatment of psychosis characterized by autism, emotional withdrawal or apathy. However, the results from of the double-blind study showed no significant difference between the placebo phase and halopemide phase. Halopemide is phospholipase D2 inhibitor: PLD1 and PLD2. Halopemide may be used as a screen to identify inhibitors of human PLD2 using an in vitro biochemical assay. It is also inhibitory at benzodiazepine binding sites.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phospholipase D1 1 Target ID: Q13393 Gene ID: 5337.0 Gene Symbol: PLD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19136975	Inhibitor 8504	21.0 nM [IC50]
Phospholipase D2 1 Target ID: O14939 Gene ID: 5338.0 Gene Symbol: PLD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19136975	Inhibitor 8504	300.0 nM [IC50]
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6291472	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
5-Fluoro-2-indolyl des-chlorohalopemide (FIPI), a phospholipase D pharmacological inhibitor that alters cell spreading and inhibits chemotaxis.	2009-03	19064628
Optimization of halopemide for phospholipase D2 inhibition.	2007-04-15	17317170
Possible individual and gender differences in the small increases in plasma prolactin levels seen during clozapine treatment.	2004-10	15365707
Regional distribution of halopemide, a new psychotropic agent, in the rat brain at different time intervals and after chronic administration.	1979-02-12	440009
Effects of halopemide, a new psychotropic agent, on the uptake of serotonin by blood platelets.	1979-02	39525
Regional localization of halopemide, a new psychotropic agent, in the rat brain.	1978-08-15	29759

Patents

Sample Use Guides

In Vivo Use Guide

(2 X 10 mg/day) and the double (2 X 20 mg/day) dose

Route of Administration: Oral

In Vitro Use Guide

The effects of halopemide on the release of 3H-serotonin, 3H-noradrenaline, 3H-acetylcholine and 3H-GABA from rat frontal cortical slices in vitro were studied and compared to those of its neuroleptic congener R29800, spiperone and haloperidol. Spontaneous 3H-serotonin and to a lesser extend 3H-noradrenaline outflow were augmented by the agents, while the effects on basal 3H-acetylcholine and 3H-GABA release were small or absent.

Name

Type

Language

NSC-354856

Preferred Name

English

HALOPEMIDE

Official Name

English

BENZAMIDE, N-(2-(4-(5-CHLORO-2,3-DIHYDRO-2-OXO-1H-BENZIMIDAZOL-1-YL)-1-PIPERIDINYL)ETHYL)-4-FLUORO-

Systematic Name

English

halopemide [INN]

Common Name

English

HALOPEMIDE [USAN]

Common Name

English

R 34,301

Code

English

N-(2-(4-(5-CHLORO-2-OXO-1-BENZIMIDAZOLINYL)PIPERIDINO)ETHYL)-P-FLUOROBENZAMIDE

Common Name

English

R-34301

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29710